Mayor Bill de Blasio’s longstanding inability to keep to a schedule speaks to a deeper chink in his political armor: He’s not just late to ribbon cuttings and memorial services. He’s late to progressive causes, too. | Michael Appleton/Mayoral Photography Office

'Make America Late Again': De Blasio's political tardiness is an enduring theme

He's late to his own announcements. He is late to his own meetings. He sometimes keeps staffers waiting while he naps in his City Hall office.

And when, after weeks of hedging, New York City Mayor Bill de Blasio confirmed Thursday he was entering a field of nearly two dozen Democratic contenders, he was late once again.

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De Blasio clocked in as the 23rd Democrat to announce a run for the presidency. In a promotional video and an announcement on Good Morning America, he cast himself as the man best suited to defeat President Donald Trump and the torchbearer of the progressive left.

“There’s plenty of money in this world; there’s plenty of money in this country — it’s just in the wrong hands,” he said in the video, repeating the same line in his interview with George Stephanopoulos.

His tardy entry into the already crowded primary underscored one of the mayor's most enduring characteristics. But de Blasio’s longstanding inability to keep to a schedule speaks to a deeper ding in his political armor: He’s not just late to ribbon cuttings and memorial services. He’s late to progressive causes, too.

“He’s a progressive who’s very conservative,” said George Arzt, a long-time Democratic operative in New York who was press secretary to former Mayor Ed Koch. “He likes to take leftist stances, but he always is late to issues. He thinks about the issues too much before he can make a decision.”

De Blasio is late to so many things, his tardiness inspired political button maker Mort Berkowitz to make it central to a de Blasio 2020 pin, which he sold for $3 a pop at a recent charity fundraiser hosted by City Hall reporters.

“Make America Late Again,” it reads, the message superimposed on a photo of de Blasio, which is, in turn, superimposed on an analog clock.

“Those who know the mayor or who have dealings with the mayor understand it, because he tends to be late all the time,” Berkowitz said.

Last year, advocates for the poor backed a cause that seemed tailor-made for de Blasio, who ran for office railing against income inequality (in his formulation, the "tale of two cities").

With subway and bus fares continuing to rise, and New York City cops continuing to crack down on farebeating in a racially disproportionate way, advocates called on the city to subsidize fares for low-income riders.

De Blasio’s board member at the Metropolitan Transportation Authority championed the cause. De Blasio resisted. Then, New York City Council Speaker Corey Johnson demanded de Blasio fund it if he wanted to pass a budget in 2018.

Following a good deal of wrangling, de Blasio ultimately agreed to fund the program. Today, de Blasio describes Fair Fares as “a major step towards a fairer and just society.”

But advocates for the program note that de Blasio was, per usual, late to the game.

“Fair Fares started moving in a serious way when Corey Johnson got involved,” said Nick Sifuentes, who helped spearhead the Fair Fares campaign when he was deputy director at the Riders Alliance.

On other issues relating to poverty, de Blasio has been similarly behind-the-ball.

As the city’s public advocate with an eye on Gracie Mansion, he was initially hesitant to back legislation that would mandate certain companies receiving city subsidies pay a “living wage” to workers. He eventually came around and used his support of the issue to go after then-City Council Speaker Christine Quinn, whom he would go on to defeat in the mayor’s race.

Chalk it up to prolonged deliberation or finger-in-the-wind political prognosticating, but Fair Fares and living wage are but two of a raft of progressive causes where the mayor has followed the progressive vanguard in the Democratic party, rather than lead it.

He was late to join the progressive effort to guarantee paid sick leave for New York City workers.

"The paid sick campaign started in NYC as early as 2008 and 2009, and [de Blasio] was not vocal or visible on the issue until later," emailed a Democratic operative who worked on the paid sick leave campaign.

It was only after activists and other politicians backed him into a corner that he came around to embracing the costly proposal to replace the jail with four smaller ones throughout the city.

He now boasts of the goal in his speeches as evidence of his action on criminal justice reform — a far cry from calling it a “noble" but impractical idea when then-City Council Speaker Melissa Mark-Viverito seized it as one of her causes.

He came late to marijuana legalization — only reluctantly agreeing with the popular progressive cause in December after his political adversary, Gov. Andrew Cuomo, indicated that he would pursue legalization at the state level, making it seem a fait accompli.

His resistance to tacking too far left on policing — he opposes loosened enforcement of turnstile jumpers for instance — is an inevitable reaction to a feud with police officers that threatened to overtake his first term in office. But it has nevertheless put him at odds with some who voted him into office on his promise of police reform.

"The mayor I endorsed in 2013 is not the mayor I've seen lately," said Public Advocate Jumaane Williams earlier this year when he was running for his current office, referring to the mayor’s record on policing and housing.

Congestion pricing — charging drivers a fee to enter Manhattan’s busiest areas to cut down on traffic and pollution — seemed a clear cause to champion for a left-leaning liberal. But de Blasio followed the same pattern: resistance until its inevitability overwhelmed him, followed by belated acceptance.

For most of the years that environmentalists and transportation advocates had been pushing for congestion pricing, de Blasio had called it a “regressive” tax. After the governor endorsed the effort and it looked like a legislative certainty, de Blasio came around.

“If you look at congestion pricing, some people would say it’s the biggest progressive accomplishment in New York City in a very long time,” said Nicole Gelinas, a transportation expert at the right-leaning Manhattan Institute. “He had a very small role in that.”

Observers note that it didn’t have to be this way. The mayor started his first term in office with a bang, fulfilling his ambitious commitment to establish universal pre-Kindergarten across the city. Since then, they lament, he’s lost that sense of momentum.

“[He has] the worst case of senioritis I’ve ever seen,” said Fordham University political science professor Christina Greer. “I’d be much more empathetic with the mayor if he was losing interest and it’s July, August of 2021, where a campaign is in full swing, he’s a lame duck, I’d understand that. But it seems as though he lost interest in the job shortly after he got reelected, and we just have a lot going on in the city.”